tert-butyl N-(2-oxoethyl)carbamate → 1-(1,1-Dimethylethyl) 3-ethyl 4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1,3-piperazinedicarboxylate

HRID 421218Notes

Reaction equation

HRID 421218 reaction equation
[N:1]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][NH:4][CH:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1.[C:19]([NH:26][CH2:27][CH:28]=O)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:23][C:22]([O:21][C:19]([NH:26][CH2:27][CH2:28][N:4]1[CH2:5][CH2:6][N:1]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:2][CH:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:20])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 114026711-tert-Butyl 3-ethyl piperazine-1,3-dicarboxylate

Product 1

HCID 592158481-(1,1-Dimethylethyl) 3-ethyl 4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1,3-piperazinedicarboxylate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To a solution of 1-(1,1-dimethylethyl) 3-ethyl 1,3-piperazinedicarboxylate [EP1486498, 2004] (2.023 g, 8.28 mmol) in 10 mL of dichloroethane was added a solution of N-boc-2-aminoacetaldehyde (1.87 g, 12.42 mmol) in 20 mL of dichloroethane. The solution was stirred at room temperature and under nitrogen atmosphere for 30 min. Sodium triacetoxyborohydride (3.32 g, 16.56 mmol) was then added and the reaction kept at room temperature overnight. The product was isolated on a SCX cartridge. 2.492 g.

Workup

  1. waitthe reaction kept at room temperature overnight
  2. customThe product was isolated on a SCX cartridge

Sources & evidence

ORD record
ord-580eb8b8be014e579fbeb09dd454aa99
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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